# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3546-9-217
_database_code_depnum_ccdc_archive 'CCDC 1408325'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;
_audit_creation_date             2015-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.28
_chemical_oxdiff_formula         'C13 H12 O3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.4655(6)
_cell_length_b                   15.5172(9)
_cell_length_c                   8.5918(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.799(8)
_cell_angle_gamma                90
_cell_volume                     1225.52(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.9245
_cell_measurement_theta_min      4.8068
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2588
_exptl_crystal_description       block
_exptl_crystal_F_000             497.6500
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4389
_diffrn_reflns_theta_full        71.0624
_diffrn_reflns_theta_max         71.06
_diffrn_reflns_theta_min         4.81
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9806
_diffrn_measured_fraction_theta_max 0.9806
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00  -13.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00   -2.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00  -24.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   24.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  6 omega -109.00  -83.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00  124.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -       54.8681   57.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  8 omega   68.00  129.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -63.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  9 omega   64.00   91.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -25.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   93.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -38.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -25.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   66.00   93.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -25.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00  115.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362 -111.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00   84.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -38.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   94.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -50.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
 16 omega  118.00  148.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  178.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   48.00  102.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -50.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
 18 omega   41.00   89.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -38.0000 -180.0000 48
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0319403000
_diffrn_orient_matrix_UB_12      0.0760356000
_diffrn_orient_matrix_UB_13      -0.1018986000
_diffrn_orient_matrix_UB_21      -0.1088682000
_diffrn_orient_matrix_UB_22      0.0563196000
_diffrn_orient_matrix_UB_23      0.0622728000
_diffrn_orient_matrix_UB_31      0.1231696000
_diffrn_orient_matrix_UB_32      0.0300644000
_diffrn_orient_matrix_UB_33      0.1408846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1756
_reflns_number_total             2330
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.1557
_refine_diff_density_min         -0.2049
_refine_diff_density_rms         0.0436
_refine_ls_d_res_high            0.8150
_refine_ls_d_res_low             9.1923
_refine_ls_goodness_of_fit_ref   1.0820
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.0820
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0941P)²+0.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1759
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_primary     direct
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.49243(18) 0.67341(10) -0.2560(2) 0.0809(5) Uani 1.000000 .
O2 O 0.90634(14) 0.48659(9) 0.15187(18) 0.0662(4) Uani 1.000000 .
O3 O 0.81545(15) 0.33388(9) 0.08400(18) 0.0694(5) Uani 1.000000 .
C1 C 0.4819(2) 0.59504(13) -0.2637(2) 0.0615(5) Uani 1.000000 .
C2 C 0.58082(19) 0.53280(12) -0.1653(2) 0.0540(4) Uani 1.000000 .
C3 C 0.7052(2) 0.54976(11) -0.0459(2) 0.0562(5) Uani 1.000000 .
H3 H 0.7356(2) 0.60606(11) -0.0200(2) 0.0674(6) Uiso 1.000000 R
C4 C 0.78192(19) 0.48109(11) 0.0330(2) 0.0553(5) Uani 1.000000 .
C5 C 0.73163(19) 0.39558(11) -0.0062(2) 0.0548(5) Uani 1.000000 .
C6 C 0.60914(18) 0.37927(12) -0.1262(2) 0.0541(5) Uani 1.000000 .
H6 H 0.57805(18) 0.32311(12) -0.1523(2) 0.0649(5) Uiso 1.000000 R
C7 C 0.53291(18) 0.44957(11) -0.2075(2) 0.0521(5) Uani 1.000000 .
C8 C 0.40079(19) 0.45075(12) -0.3386(2) 0.0549(5) Uani 1.000000 .
C9 C 0.3632(2) 0.54428(13) -0.3760(3) 0.0624(5) Uani 1.000000 .
H9a H 0.268(2) 0.5590(13) -0.352(3) 0.075(6) Uiso 1.000000 .
H9b H 0.364(3) 0.5584(15) -0.492(3) 0.087(7) Uiso 1.000000 .
C10 C 0.9657(2) 0.57098(14) 0.1882(3) 0.0718(6) Uani 1.000000 .
H10a H 0.9873(17) 0.5957(4) 0.0941(6) 0.1077(9) Uiso 1.000000 GR
H10b H 0.8964(8) 0.6066(3) 0.223(2) 0.1077(9) Uiso 1.000000 GR
H10c H 1.0534(10) 0.56730(18) 0.2716(14) 0.1077(9) Uiso 1.000000 GR
C11 C 0.7704(2) 0.24653(13) 0.0548(3) 0.0784(7) Uani 1.000000 .
H11a H 0.7691(19) 0.2317(4) -0.0540(7) 0.1176(11) Uiso 1.000000 GR
H11b H 0.8370(11) 0.20948(16) 0.1263(15) 0.1176(11) Uiso 1.000000 GR
H11c H 0.6746(8) 0.2396(3) 0.072(2) 0.1176(11) Uiso 1.000000 GR
C12 C 0.3303(2) 0.38265(14) -0.4131(2) 0.0635(5) Uani 1.000000 .
H12 H 0.3654(2) 0.32827(14) -0.3782(2) 0.0762(6) Uiso 1.000000 R
C13 C 0.1977(2) 0.38762(16) -0.5496(3) 0.0758(6) Uani 1.000000 .
H13a H 0.1208(2) 0.41642(16) -0.5128(3) 0.0910(8) Uiso 1.000000 R
H13b H 0.2203(2) 0.42260(16) -0.6341(3) 0.0910(8) Uiso 1.000000 R
C14 C 0.1439(4) 0.3032(2) -0.6170(4) 0.1317(15) Uani 1.000000 .
H14a H 0.060(2) 0.3113(2) -0.704(2) 0.198(2) Uiso 1.000000 GR
H14b H 0.2185(12) 0.2746(9) -0.656(3) 0.198(2) Uiso 1.000000 GR
H14c H 0.118(3) 0.2687(7) -0.5352(11) 0.198(2) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.221(2) . ?
O2 C4 1.365(2) . ?
O2 C10 1.430(2) . ?
O3 C5 1.361(2) . ?
O3 C11 1.425(2) . ?
C1 C2 1.465(3) . ?
C1 C9 1.515(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.388(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.423(2) . ?
C5 C6 1.379(2) . ?
C6 C7 1.399(2) . ?
C7 C8 1.470(2) . ?
C8 C9 1.511(3) . ?
C8 C12 1.330(3) . ?
C12 C13 1.501(3) . ?
C13 C14 1.473(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C4 116.41(15) . . ?
C11 O3 C5 117.33(15) . . ?
C2 C1 O1 126.34(19) . . ?
C9 C1 O1 126.23(18) . . ?
C9 C1 C2 107.43(17) . . ?
C3 C2 C1 127.84(18) . . ?
C7 C2 C1 109.79(17) . . ?
C7 C2 C3 122.37(17) . . ?
C4 C3 C2 118.17(17) . . ?
C3 C4 O2 125.50(17) . . ?
C5 C4 O2 114.55(15) . . ?
C5 C4 C3 119.94(17) . . ?
C4 C5 O3 113.86(16) . . ?
C6 C5 O3 124.65(17) . . ?
C6 C5 C4 121.49(16) . . ?
C7 C6 C5 118.14(16) . . ?
C6 C7 C2 119.84(16) . . ?
C8 C7 C2 110.72(15) . . ?
C8 C7 C6 129.44(16) . . ?
C9 C8 C7 106.81(16) . . ?
C12 C8 C7 126.63(18) . . ?
C12 C8 C9 126.54(17) . . ?
C8 C9 C1 105.22(16) . . ?
C13 C12 C8 124.4(2) . . ?
C14 C13 C12 114.1(2) . . ?

_olex2_date_sample_data_collection 2014-05-07
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
(E)-5,6-dimethoxy-3-propylidene-2,3-dihydro-1H-inden-1-one
_chemical_melting_point          395-397
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
